Amyl nitrite

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Amyl nitrite are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Amyl nitrite?

The molecule Amyl nitrite presents a molecular formula of C12H12N4O3 and its IUPAC name is pentyl nitrite.

Amyl nitrite is a molecule with the chemical formula C5H11NO2. It is a clear liquid at room temperature and has a pungent, sweetish odor. It is used as a reagent in organic synthesis and as a solvent. It is also used as a recreational drug, commonly known as "poppers.".

Amyl nitrite is produced by the action of nitrous acid on amyl alcohol. It is also formed by the decomposition of certain esters, such as amyl acetate..

The molecule consists of a five-carbon chain with a nitrogen atom bonded to the second carbon and an oxygen atom bonded to the third carbon. The nitrogen atom has a lone pair of electrons, which gives the molecule a trigonal pyramidal shape..

The molecule is polar, with the oxygen atom being more electronegative than the nitrogen atom. This results in a dipole moment, with the oxygen atom having a partial negative charge and the nitrogen atom having a partial positive charge..

The boiling point of amyl nitrite is 34°C and the melting point is -45°C. The molecule is soluble in water and is commonly used as a solvent in organic synthesis..

Amyl nitrite is used as a recreational drug due to its psychoactive effects. When inhaled, it produces a rush of heady sensations and a feeling of euphoria. These effects are caused by the release of nitric oxide, which acts as a vasodilator and increases blood flow..

The effects of amyl nitrite typically last for a few minutes and are followed by a feeling of relaxation. There is a potential for abuse and addiction with this drug, and it should be used with caution..

3D structure

Cartesian coordinates

Geometry of Amyl nitrite in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Amyl nitrite CULUWZNBISUWAS-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Amyl nitrite

 

Molecule descriptors

 
IUPAC namepentyl nitrite
InChI codeInChI=1S/C12H12N4O3/c17-11(14-8-10-4-2-1-3-5-10)9-15-7-6-13-12(15)16(18)19/h1-7H,8-9H2,(H,14,17)
InChI KeyCULUWZNBISUWAS-UHFFFAOYSA-N
SMILESO=C(Cn1ccnc1[N+](=O)[O-])NCc1ccccc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-pentyl nitrite
  • 463-04-7
  • A0455
  • A19477
  • A802198
  • AI3-25184
  • AMY3989
  • Amyl nitrite
  • BRN 1701241
  • CCRIS 763
  • D88264
  • DB01612
  • DSSTox_CID_4522
  • DSSTox_GSID_24522
  • DSSTox_RID_77442
  • FT-0622367
  • H2HUX79FYK
  • HSDB 8468
  • LS-13085
  • MFCD00036132
  • N-Phenyl nitrile
  • NCGC00260444-01
  • NITRITE DE PENTYLE
  • Nitrous acid, pentyl ester
  • Pentyl alcohol, nitrite
  • Pentyl nitrite
  • Pentyl nitrite, AldrichCPR
  • Pentylnitrite
  • Q412350
  • STL268844
  • UN 1113 (Related)
  • amyl 1 nitrite
  • n-Amyl nitrite
  • n-Pentyl nitrite
  • n-pentylnitrite
  • nitrous acid pentyl ester

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC20230701
  • CAS-463-04-7
  • UNII-H2HUX79FYK
  • AKOS015853631
  • DTXSID3024522
  • CHEMBL3188202
  • CHEBI:55344
  • Tox21_202898
  • EINECS 207-332-7
  • SCHEMBL34065

Physico-Chemical properties

IUPAC namepentyl nitrite
Molecular formulaC12H12N4O3
Molecular weight260.249
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity69.41
LogP2.0
Topological polar surface area92.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.